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Random old emails delivered to recipients after a restart of Widows SBS 2003 running Exchange SP2

I have an odd problem that as of yet I have been unable to isolate.  We've begun to see that random emails seem to get stuck somewhere and are suddenly sent out when we restart our Windows SBS 2003 server running Exchange SP2.  When we haven't restarted for a month or two, we've seen emails sent out that are up to two months old.  There is no pattern.  There are some people that I may send 4 emails a day and when we restart they mention that a couple of old emails suddenly appear that were never sent .  It therefore isn't an isse of an undeliverable address.  Other users have reported similar scenarioes after we restart.  

It is difficult to give an accurate assessment of how often this happens but I suspect that it is less than 5% of the emails and i likely less than 1% of the emails we send.  Unfortunately if the one that gets stuck is important and we don't get any notifcation of a problem we assume it was sent.

Has anyone seen anything like this before and / or do you have any suggestions on what might be causing this and how I might go about tracking and correcting the issue.  

For now I've resorted to restarting the server once a week in order to flush out the stuck emails more often.

Thanks Mike
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Mike93110
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Mike93110
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aa230002Commented:
Are these mails getting delivered twice? like delivered as and when they were sent originally and after 2 months after reboot, they get re-delivered.

when you see these emails in your Outlook, what is the "received at" time stamp on the email?
Is it happening only to the internal mails or also the mails coming from outside world (internet). Check the header of the mail. right click on the mail - options.

Which Anti-virus you are using? make sure its updated.

thanks,
Amit Aggarwal.


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Mike93110Author Commented:
The emails appear to have not been delivered previously and they are time stamped with the date they were originally sent.  It appears to be happening primarily to emails sent out from our server to other servers.  It would appear that some emails are just not being delivered at all.  I have direct knowledge of some text only emails that do not include attachments that have not gone through.  Forwarding them a few hours later however they work fine.  Again this is happening randomly and for less than 5% of our emails.

I am currently running Symantec SMS for Microsoft Exchange v 4.5.  I hadn't thought that this could be the problem.  Are there better Exchange based Anti-Virus applications out there that I should look at?
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aa230002Commented:
antivirus program can be a culprit, but Symantec SMS for Microsoft Exchange v4.5 should be fine. I just wanted to say that make sure it is updated if any updates or fixes are available for this product from Symantec.

Before you restart your server once in a week, Do you see any mails stuck in the queue? if yes, try to track those messages using message tracking center and see, if it tells you why the mails are sitting there.

I have another thought, i would like to do the database maintenance once. An offline defrag and isinteg -fix to fix all logical corruptions in the database if any. You need a downtime for this depending on the size of the database and make sure that you take full backup of the server before you start this process.

How to defragment with the Eseutil utility (Eseutil.exe)
http://support.microsoft.com/default.aspx?scid=kb;en-us;192185

How to identify logical corruption problems in Exchange Server
http://support.microsoft.com/kb/828068/en-us

thanks,
Amit Aggarwal.
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Mike93110Author Commented:
I've reinstalled Exchange SP2 and have updated all my Symantec Products to the latest version.  After I have a chance to do a full system backup I will follow up on with the defrag and the look for logical corruption.  Thanks.  Hopefully this combination will take care of things.
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